


Fake Bittersweet Love

by theduchessofhell



Category: Supernatural
Genre: Alternate Universe - Human, Alternate Universe - Modern Setting, Alternate Universe - Romantic Comedy, Angst, Dysfunctional Family, F/F, Fake/Pretend Relationship, Flirting, Fluff, M/M, Sleepovers
Language: English
Status: In-Progress
Published: 2014-06-20
Updated: 2014-09-07
Packaged: 2018-02-05 12:40:19
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 13,297
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1818868
Author URL: https://archiveofourown.org/users/theduchessofhell/pseuds/theduchessofhell
Summary: <blockquote class="userstuff">
              <p>Anna is a sweet girl with a rebellious side.  <br/>Ruby is a rebellious girl with a sweet side.  <br/>They plan to be in a fake relationship.<br/>These two girls find their plan to be fun, but they didn't realize there'd be awkward tension, silly moments where they're both guessing if this is part of the 'fake relationship' act or not.  Because, surely, these blushes and butterfly nonsense is acting, right?</p><p>It's all actually kind of bittersweet.....</p>
            </blockquote>





	1. Little Red and Wolf.

**Author's Note:**

> My first fic. I hope it's good. This is for tumblr user haelstorm who wanted a cutesy femslash fake relationship fic. This'll be multiple chaptered. Plus, the annaby ship needs more love!

**Summary for the Chapter:**

> Anna has to go face her family, even though she's made it sure that she wanted to leave and they made it sure they won't take her back. Ruby decides to be Anna's pretend girlfriend.

Anna stares down at the paper with wide frightened eyes, as if she was seeing a ghost. She pauses for at least 20 seconds, staring down at the page with intensity that can kill someone.

She thought that everything in her life wasn't complicated anymore. But every time she is proven wrong.

Like the fact that she can't tell if she wanted to run away or if her family is shunning her. Or if the only reason why they see her is to push her away further.

The terrible part is that it works. It really does work.

And every time she makes sure she pulls a stunt that'll make her have the last laugh. It's almost as if its competition.

So Anna Milton still has the same expression on her face when she's at the bar. This time her face switches to anger. 

She clutches the cold beer in her hand like it's a weapon.

"You trying to freeze you hand off?" Jo finally stops giving doe eyes at the flirtatious girl, Charlie, that just took a seat near Anna.

Anna just gives the blonde girl a look and Jo puts her hands up in defense.

Charlie rolls her eyes and nudges Anna with her shoulder, "Come on, Milton. What's bugging you this time?"

Anna shoves the perfume sprayed, gold lettering invite she had received that afternoon towards them.

Charlie reads and Jo tilts her head to catch a glimpse.

"At least it isn't from someone you hate. Plus, he'd understand if you don't go." Charlie mutters.

"Yeah but there will be people there who hate me and that I hate."

"Cas would." Jo smiles once she's done reading. "So basically he thinks it'll be safe if he invites everyone for the holidays."

"I've heard stories, and I'm not sure if they're exaggerated, but they all end in rage and tears." Charlie sighs.

"Not an exaggeration." Anna runs her hand through her red air nervously.

"You not going then?" Jo questions while cleaning a few cups with a rag.

Anna hesitates," I-It's Castiel, though. He's the only one I can stand."

"Minus the guilt card, what's your answer?" Charlie turns in her seat.

"I don't know." Jo uses a sing song voice, "Last time you came back, they still thought you were in a 'rebellious phase.'"

"I haven't done anything brutal!" Anna protests. Sure, she doesn't obey her family, but it's only because she has her own different beliefs. That doesn't make her...bad.

Anna is a sweet girl with a rebellious side. But that doesn't make her bad.

Anna is a sweet girl with a rebellious side. But she has major problem.

1) Every time she sees her family, they have a bunch of boys they want her to meet (and eventually marry)

2) Everyone there always judges he lifestyle. She needs someone who has a similar one and so she can prove to them that she isn't a failure.

3) She wants to see the look on their faces as soon as they see her in a relationship. She wants to see their reactions.

4) Secretly, she doesn't want to do this alone.

"I need a girlfriend." Anna murmurs to herself. "A fake girlfriend."

"I call dibs on the chick with the movie collection." Jo calls out.

Charlie smiles and adds, "I call dibs on the chick with the knife collection."

Anna doesn't know who would do a thing.

She wasn't paying attention to anything around her anymore. 

All the girls she's friends with wouldn't ever do a great job at acting this part, plus her family would know who they are.

With a blink of an eye, Jo and Charlie are greeting a girl who walks into the Roadhouse.

The girl walks in and thunder roars.  
The girl strides to the bar and its like lightning lit the room. In high heels, a tight black dress, and a grin that can kill, she sits on the seat next to Anna.

The stranger looks Anna up and down. As soon as those beautifully devilish eyes meet Anna's, she knows who she's staring at. “Hey, you’re Ruby, right?”

"Yeah, and you're the famous Anna Milton." the girl mocks. Anna gives her confused look. She sighs and explains, "A princess like you growing up to be the family rebel. I like that."

"S'nothing compared to what you are Ruby." Anna scoffs.

"Oh." Ruby turns to face her in her stool, "And what may I be?"

Anna looks down at her drink and then back to the other girl, "......Satanic. Demonic......"

Ruby smiles at that surprisingly. She chuckles and turns to face the bar again, "So, Little Miss Angel knows who I am...…" she sips the drink.

"The things you do. They're impressive…..and a little scary."

"I'm just like the rest of them."

"No. I think you’re pretty cool." Anna nudges her with her shoulder and immediately pulls back. She turns her head and feels her face get hot.

Ruby leans into the touch and Anna doesn't try to lean back more. Even if she wanted to, she'd fall off the barstool.

One moment, the four girls are talking about something random and normal. The next moment, Anna tries to sneak another glance at Ruby. Then she sees Ruby pulling her arm away from some muscular man.

"Ruby, I thought we were cool now." the man's soft voice fuels a fire in Anna's rage.

"Last time I checked, I left your ass on the curb. Literally." Ruby calmly responds through a clenched jaw.

"Babe, come on. You know you just love me. You can't help it." he slips his arm around her waist.

Ruby easily pushes him away but he tries again. This time Anna grabbed his hand tightly. His hand can't pull out. "Excuse me." Anna innocently looked up at the tall man, "If you'd like to keep your hands, please take them off my girlfriend."

She looks back to see Ruby smirking and biting her lip trying not to laugh.

The guy looks at Ruby, then back at Anna. "I don't want any trouble with two psychotic lesbians." He puts his hands up and storms out the bar.

Anna feels glad about that but then pauses when she feels Ruby breathe on her neck. Anna turns around, "That happen often?"

Ruby nods, "That was smart of you." She refers to the recent situation.

"The family that ignores me forces any boy they think is decent onto me. Decent meaning boring. Plain."

"I understand. I can't say your folks are fun people."

"I actually have to see them this weekend. It's going to suck." She sighs. "Too bad I won't have a fake girlfriend then. We would mess up their minds." She giggles.

"I'd do it." Ruby quietly says and rocks on her heels. She feels like she messed up so she says, "I've done it before, it is really fun."

"Hey, Ruby?"

"Yes, Anna?"

"Would it be odd if a Milton asked to be your pretend girlfriend?"

"Considering I hate all of the Milton's and their friends, I'd have punched someone already." Ruby's smile still stays.

"You're different though. You have at least two-fifths of a heart."

Ruby chuckles, "Us girls, we have to watch each other's backs. And Anna," Ruby's grin and eyes fall down to the ground. She almost looks small. Almost, "you're actually really cool."

"So is that a yes?"

"Buy me a drink or french fries before we meet the family." Ruby jokes and her tone......is warm like a bonfire.

Anna's eyes glisten with delight, and Ruby goes back to looking seductive and scary, "But you still aren't a complete badass yet."

 

~~~~~~~~~~~~~~~

 

Anna is a sweet girl with a rebellious side.

Ruby is a rebellious girl with a sweet side.

This can either go terribly or perfectly.

More of the former.

Anna bounced on her feet waiting for her brother to open the door.

She'd come here on a plane, not with Ruby, though. And it's terrifying to think that maybe Ruby had planned something horrific.

Or maybe it's a joy to think that.

Once the door opens, she's dragged across the house to the back door.

Castiel's garden has always been nice and beautiful. Now it makes Anna sick that there are small circular tables filled with her family members.

Cross that out: Relatives, not family.

She freezes when she spots a table where she can see all their faces except one who she sees the back of.

The girl turns around and gets up. She hands Anna a tall thin glass of wine, "Hello, Anna."

"You came early, Ruby." Anna keeps her calm in front of her family.

"I needed to chat up your family, of course." Ruby smiles and gestures to her family. Ruby laughs and Anna knows the acting has started and she doesn't know when it'll stop.

Ruby opens a chair for Anna to sit in. Anna feels her shoulder touch the back of Ruby's hand and they both pull apart awkwardly.

"So, Anna," Hester lips smile forcefully, "still doing your.....job?"

“Yes, still a full time artist." Anna grits her teeth together.

"Oh." Is all she replies. She seems disappointed but amused.

Michael coughs to break the tension, "How'd you two meet?"

"Anna's artwork caught my attention actually." Ruby defends her from the previous comments. Anna's positive thoughts fall when she realizes Ruby has never seen her art.

"Do you do art, too?"

"No. I was modeling for an art class that Anna attended. They were drawing figure sketches."

Michael nods, "It must've been a great sketch if you liked it more than the others." Anna can't tell if he knows something's off and is just mocking them or if he's suddenly being nice. He turns to Anna, "You should show us your artwork sometime."

"Maybe during the family dinner tomorrow." Anna replies.

"Excuse me. I'd like to speak to Anna alone." Ruby grabs Anna's arm and tugs her to the other side of the garden. "They don't know we're 'together.'"

"What?" Anna exclaims.

"They just believe we're good friends." Ruby smirks, "Wait till they introduce you to those boys and then learn the truth."

"Breaking the news in the worst way possible, I like that." Anna returns the cocky expression. They stare a second too long at each other and both of then turn away like blushing brides.

Anna already spots her uncle bring over a couple of young men to her. "Good to see you, Uncle Zachariah."

"Anna, I would like you to meet some of my employees." His grin is not comforting at all.

"Wouldn't you like to meet my girlfriend first?" Anna speaks up.

"Girlfriend? Don't tell me this is part of your........phase!"

"It is not. She's dear to me. Is there something wrong with her?"

"First of all, she's a she. Second of all, even if you are in a relationship, it's probably with a disgusting terrible fool."

"Close." Ruby appeared from behind Anna. The way Ruby stands with one foot in front of herself so she's slighting in front of Anna, makes the girl feel safe.

What ever bum her family believes Anna would be with, it is the opposite of Ruby. Sure, her attitude is probably seen as rude, but the way she looks and stands is amazing.

Surely Anna's relatives wouldn't expect a girl. But they would never had thought of this confident, intimidating successful looking woman to take a liking to Anna.

Anna made a quick move to slip her fingers around Ruby's. She tries to make it look natural, but it ends up feeling embarrassing.

Ruby tenses, she's freezing under Anna's hand holding and if Anna said she didn't blush, it's the biggest lie of the century.

Their bodies move normally but Ruby's right arm and Anna's left arm decide to stay as still as possible.

"Hey there, sweetie." Ruby nuzzles into Anna's hair, making an audible smooch sound.

"I was just talking about you. My uncle would like me to meet some of his friends." Anna innocently looks to Zachariah.

“Yes, I still do want her to meet them. They're very convincing and hopefully can talk some sense into you." His threats lie beneath his friendly tone. "It's never too late to change your mind."

"I disagree." Ruby tells him, "It's far too late for Anna and I to lie in bed all day instead of putting on clothing and come to this place."

"Please, Anna, I know you mustn't really care for someone like....her." Zachariah ignores the other woman.

"Well, I brought her here. What else do you want me to do? I thought you hated public affection."

"We aren't out in public, are we?" he argues.

"I just thought you'd be uncomfortable by our admiration for each other." Anna grins. Ruby giggles into her neck. It tickles Anna and she hopes her strands of hair cover her flushing face.

"Is this the niece you were talking about?" A young man asks Zachariah and he looks Anna up and down.

“Yes, this is Anna and her friend."

"Girlfriend." Ruby corrects and the two men ignore the comment. Ruby watches in annoyance as the young man kisses Anna's cheek in a greeting.

Ruby scoffs and snorts, "You call that a kiss. She deserves more than a peck from her uncle's man slave."

Anna can't help but think her tone sounded genuine. Anna can't help but feel proud of Ruby's irritated remarks.

"Come on, babe. Let's go meet more of your relatives."

 

Thankfully, Anna finds Castiel at another table. She hurries off to see him. The feeling of Ruby's strong fingers linger.

"Anna!" Castiel throws himself at his sister, "I can't believe you came." His muffled voice speaks into her hair.

He spots Ruby standing and watching at a distance.

"You brought a guest?" Castiel slowly let's go.

“Yes, is that okay?" Anna tries to sound sorry.

"No, no! Of course not." the two siblings share a grin.

Anna gestures to Ruby and the brunette girl moves closer hesitantly, "Brother, this is my girlfriend, Ruby. I decided to bring her along so the whole family knows her."

"That's very brave of you to do, Anna. Nice to meet you, Ruby." Castiel greets her.

"Hi. Castiel, correct?" Ruby shifts her weight to a different foot, "I've heard much about you. I actually only know you, the rest are...."

"Oh, yes, our other relatives can be a bit difficult at times. I hope you still have a nice stay." Ruby isn't sure how to respond to this kind of host but it's okay because he turns back to his sister.

"Castiel, do you mind if we skip tonight and go to bed? I'd rather have only one dinner with the whole family tomorrow."

"Feel welcome to do so. I'm so happy you came." Castiel hugs her again and she hugs back actually feeling satisfied of coming here.

Anna nods and takes Ruby's hand again. She feels Ruby flinch at the touch and Anna immediately let's go.

Anna takes a step away from her, but Ruby reaches for the pale girl's hand allowing Anna to guide her.

Anna leads them to an extra guest room in Castiel's house.

She knows that most of her family booked nice hotel rooms or have a house here. So she doesn't have to worry about seeing them in the morning and daytime.

"Hey, you okay with me sharing a bed with you?" Ruby asks.

“Yeah, but, I sprawl out in my sleep."

Ruby chuckles, "Me, too. Also, don't tell any one or I'll hunt you down," Anna somehow knows it's not an empty threat, "I sleep cuddle."

"The big bad wolf is actually a puppy, huh?" Anna mocks and feels a pillow to her head.

"I don't know. Maybe I should be worried. I know Little Red Riding Hood isn't so innocent." Ruby pokes Anna's stomach.

"I'm actually tired. I better get some sleep, my family are morning people so I won't have any tomorrow."

"What? I'm a night person! I can't have people ruining my sleep!"

"Deal with it, wolf." Anna pulls the blanket around her and curls up.

After a few minutes of resting, Anna opens one eye to find a small light next to her, "Rubes?"

"Yeah?"

"Why aren't you asleep?"

"I said I'm a night person. I'm just doing a little reading."

Silence.

"Want to see my sketches?" Anna pokes her head out of the blankets.

"Yeah."

Anna jumps out of bed excitedly and grabs her sketch pad. She tosses it onto Ruby's lap and Ruby opens it right away.

Anna studies Ruby's expression. Each drawing, Anna watches the other woman's pupils, lips, breathing to see what she thinks about it.

"Well?"

"Your drawings. They're beautiful."

Anna didn't feel like she needs a blanket any more. And she isn't sleepy any more. She feels like she's burning and full of sugar.

But it's a good feeling. Ruby turns of the small light, but Anna caught a glimpse of the blush before she his it.

"Goodnight, Anna." she whispers.

"G'night, Ruby."

 

~~~~~~~~~~~~~~~

 

"Why are they sleeping so far apart?"

"You know Anna's always been a mover. Ever since she was little."

"Yeah, but from previous boyfriends, she's also way too affectionate."

"Yeah, gross."

"Do you think they'll wake up?"

"I dunno."

Anna blinks and she sees the white ceiling. It's blurry so she blinks a couple more times and then spots two figures.

Two figures she hasn't seen in years.

Two figures that can tell when Anna's lying no matter what she's lying about. Even through letters, text messages, through other people, these two can tell what's a lie because these two know how to lie.

"Dude, Anna grew up." the shorter figure spoke.

"And got ugly." the other one tilts his head. The short one laughs.

"Gabriel! Lucifer!" she screams their names in horror and sits up. Ruby is alert right then.

"Hey, its Ruby!" Lucifer points at the brunette.

"Lucifer!" Ruby is now scared.

Lucifer's amused grin becomes dark, "What the hell are you doing sleeping with my little sister?"

"You're her brother? You're a Milton?"

"Not a Milton." Lucifer shakes his head.

"Milton is my mother's last name." Anna mutters to Ruby.

"Why are you two?" Gabriel moves his hands around, gesturing at the whole situation.

Ruby automatically smirks and leans over to Anna, "Good morning, hun." she whispers into Anna's ear and it sends shivers down Anna's spine.

Anna feels like a teenager again when her brothers spotted her with her boyfriend in the school hallways. Doing these thing in front of her brothers aren't a very smart thing to do.

It seems very fake when Anna presses her lips onto Ruby's neck. Her delicate lips barely brush against Ruby's sensitive spot on the neck.

Anna doesn't want to look at her brothers'. Her hands are literally shaking and trembling in nervousness.

When she looks back, Gabriel and Lucifer look as confused as Castiel did when he first watched 'inappropriate content'.

"You're dating Anna." Lucifer points accusingly at Ruby. Ruby's head hits the bed's headboard.

"Yes, she is. I'm not 14 any more, Luce." Anna rolls her eyes at him.

He points to her and Anna freezes, remembering what temper her brother has. "Watch your attitude, sis." he walks out of their room.

Gabriel low whistles, "So, Lucy's still the same."

"Gabe!" Anna gets on her knees and scoots towards the edge of the bed to hug him, "Why'd you come?"

"Same reason you and Lucifer did." he hugs her back. She misses his low voice and humor. She misses his funny comments and how he can be seriousness when he's taking care of them.

"This is Ruby." Anna turns we body to the other girl.

"Yeah, I know." Gabriel smirks, "Weren't you dating Lilith the last time I saw you?"

"So?" Ruby replies. Gabriel looks from Ruby to Anna and back again.

"Don't you dare say anything, Gabriel." Anna's voice goes low and harsh. If Ruby isn't impressed, then she sure is slightly aroused although she'd never admit it.

"Only on one condition." he puts a finger up and then points it towards Ruby with a wiggle in his finger, "Give me Sam Winchester's phone number."

"I don't have it." Ruby says. Gabriel's eyebrows go up. She stares at him for a few more moments before throwing a piece of paper at his head.

He catches it instantly without looking away from the girl, "Someone's heading upstairs, better get your act together." he warns them before walking out the door.

Anna doesn't know whether to sit up or lie back down. Ruby already knows what she's doing. Anna finds herself with a lapful of Ruby one second and the next second she sees the door swing open through Ruby's dark hair and allows Ruby to push her lips against her own.

She knows that Ruby knows that they could just kiss easily since their morning messy hair is covering most if their faces. They don't even need to kiss for real. But Ruby decides to catch Anna's bottom lip between her teeth.

Every single one of Anna's past lovers had been gentle, tender, and fulfilled every one of her needs.

And it'd be an understatement when Anna thinks that she doesn't mind Ruby's grip tugging her hair enough to feel good and not hurt.

She heard a cough, and she felt Ruby’s lips pull away slowly. Surprisingly, Anna chased after her lips and places one last kiss on Ruby’s jaw. Ruby gets off her and looks self-conscious.

Anna also has the same look of shame and it’s not the acting that makes her look guilty.

 

Dean Winchester looks at the two girls, “Um…….”

“Yes, Dean.” Ruby looks down at her hands. She plays with the ring with a couple of symbols on them. She looks up at Anna and when Anna does the same, the two immediately cringe away.

“Cas made breakfast. He’s trying to save some for you two but Gabriel and I are going to eat it all.” Dean tries his best to not look like he interrupted something.

“Go tell your boyfriend we’ll be right there.”

“Not my boyfriend.” Dean mutters.

“And tell your future brother in-law to save us some syrup.” Ruby adds.

“Cas and I won’t get married.” he defends himself poorly.

“I didn’t say you and Cas’ll get married.” Ruby whispers, “You should watch out for little Sammy when he meets the candyman.” she winks.

Dean’s jaw clenches and he runs down the hall yelling.

Ruby hears Anna giggling. She looks over and doesn’t notice she’s smiling at the sound.

Anna returns the smile and for once, the fire in Ruby’s heart isn’t burning her. 

 

 

It’s finally warm.

 

**Notes for the Chapter:**

> This is my first fic I've ever posted. It's for tumblr user haelstorm who wanted a femslash fan fiction about pretend girlfriends. Also, I believe Annaby needs more loving.


	2. Sweet Young Things and Rotten Hearted Hotties

**Summary for the Chapter:**

> Anna and Ruby get ready for dinner tonight. Anna's nervous to see her family and Ruby's nervous about this fake relationship. She's actually anxious about the 'fake' part now.

Anna hops out of her bed and walks towards the door. She opens it and is about to step into the long hallway.

"Wait!" Ruby grabs the girl's arm and spins her around to face Ruby. Ruby licks her lips, concentrating on messing up Anna's hair to look like it's been in an inappropriate situation.

Ruby runs her fingers through Anna's soft, thin red hair one last time. Anna will never get tired of how Ruby's fingers curl.

"There." Ruby grins. They both run down the hall, or skip down it, to the open living room and kitchen.

Castiel's home is very spacious with high ceilings but it still manages to look small and cozy.

"Good morning, Anna, Ruby." Castiel greets the two girls with plates. They pile some pancakes on top of their plates and Anna steals the maple syrup from a sad Gabriel.

He pouts and makes grabby hands at the bottle while Anna sticks her tongue out.

Lucifer stares at his own pancakes with narrow eyes like a predator targeting it's prey.

Dean looks between the whole family with two full cheeks of food.

Ruby and Dean share a confused look.

 

Anna spots another person sitting beside them all. The tall man looks guilty like a puppy that just got yelled at.

"Hiya, Sammy." Ruby waves at the boy.

"It's Sam. S'not Sammy." he pushes around his food on the plate and tries to concentrate on concentrating.

"Gabe!" Dean kicks the man.

"Ow! What?" Gabriel replies.

"He's my baby brother that's gross!"

"Cas is my baby brother, too!"

"Yeah but Cas is a little older than me and you're older than Cas! Which makes you an old guy!"

"Wow, Dean-o. You're great at math, aren't ya?"

"Did Dean just admit to liking Castiel?" Anna stops them both.

Lucifer finally looks up at Dean and they all stare and wait, "Are you trying to court my little brother, Dean?"

"Oh, shit." Ruby breathes and Anna squeezes the girl to make her shut up.

Castiel coughs and they all turn their attention on him.

"Well, tonight's Thanksgiving, so you are all going to help me get ready for dinner." Castiel explains, "Anna, Ruby, can you two please go to the grocery store and get everything on my list?"

"Of course." Anna agrees.

Dean adds, "Anna, Ruby, no quickies in the car. We'd rather get everything done in time."

"As long as you and Cas don't do anything on the kitchen counters." Ruby promises.

Castiel rolls his eyes in time with Anna's and he ignores them. He politely asks Sam, "Would you mind watching Lucifer when you two help me? I don't trust him to-"

"Sorry, brother. I have some people to visit while I am here." Lucifer doesn't even look up at them.

"Nevermind. Would you make sure Gabriel does not try any.........'new recipes' when he bakes?" Castiel pleads.

"Cassie, how dare you accuse me of such a thing?" Gabriel sarcastically comments.

"Cassie?" Sam snorts.

 

~~~~~~~~~~~~~~

 

~~~~~~~~~~~~~~~

 

Anna wasn't usually insecure about changing her clothing in front of others. She hasn't felt uncomfortable about it since middle school when she first had to change in the locker rooms.

But she's taking off her clothing slowly and carefully when Ruby's standing on the other side of the bed.

Ruby's doing it just fine and Anna doesn't want to think about it, but the way Ruby naturally slides out of her shirt makes her feel hot in the neck.

Ruby spots the nervous girl and believes that Anna is acting like this because of Ruby being in the same room. "Do you want me to change in the bathroom or something?"

"No, no!" Anna blurts out. It sounds desperate but really, Anna doesn't want to seem rude in front of Ruby. She wants Ruby to feel welcomed and in place.

Ruby smirks to Anna's surprise, "Eager girl." she mutters loud enough to tease Anna.

 

~~~~~~~~~~~~~~

 

"How about popcorn?"

"Popcorn?"

"Yeah, thanksgiving could have some popcorn." Anna waves around a box. Ruby shakes her head and laughs.

"Okay, next in the list is potatoes." Anna runs to the aisle and grabs a bag.

She runs all the way back to the cart since Ruby half walks while pushing the cart unenthusiastically

"Have you actually ever modeled for an art class?" Anna asks curiously.

"Yeah." Ruby nods, "A few times, for some money and it was a friend's class so I helped her out."

"A girlfriend?"

"No. Just a friend. Surprising, I know."

"Do you think we need to act out here, too?" Anna asks. She says it like she hopes not but a tiny piece of her wouldn't mind if they had to.

"It's a very small town, you think they'll be people here than know one another?" Ruby answers with a question.

"Well, when you're Anna Milton, the one that mutually left and got kicked out of the family, people will talk...."

"Oh, okay then." Ruby swallows down any bit of worry away. She sticks out her hand in an unsure way. Anna stares a hole into it, "Take it, weirdo."

Anna does and Ruby swings their arms a little. At first the brunette has to make sure it's timed and at the right pace. It looks sturdy and tense. But after a few swings, Anna and Ruby's arms are relaxed and in a rag doll mode.

It's actually natural.

"Do you usually like stuffing in your turkey?" Anna asks eventually while they pick up more supplies. She's just trying to make conversation.

"Yeah, a lot more than normal."

"I can make sure yours is extra stuffed."

Anna turns her head quickly to see Ruby dropping the food she's holding in her hand. Ruby catches it and fumbles with it a lot.

Then Anna realizes what she semi implied and her neck matches her hair now.

Ruby clears her throat and looks around like she's making sure no one notices. She walks over to the cart to put the things in. "Save that type of talk for desert, babe." Ruby whispers before passing by her to get to their cart.

Anna shakes from the shivers down her arms. The light hairs on her arms stick up and she has goose bumps from that voice.

"Is that it?" Ruby's normal, but still hypnotizing, voice gets Anna to return from her daydreams.

She looks over the list once more before nodding.

Once they bought everything, they go drive back to Castiel's house.

But then the two decided to buy some fast food since they won't be eating anything till later tonight.

"Can I have three large fries and two milkshakes?" Ruby is out of her seat and leaned over Anna to order. "One chocolate and one...."

"Vanilla." Anna whispers.

"Vanilla." Ruby yells to the machine. She turns backwards to face Anna, "I knew you were vanilla."

"In another universe maybe." Anna laughs.

"Here, eat." Ruby pokes three crunchy fries against Anna's pale cheek.

Anna moves away to her left, "Stop, I'm driving."

"Open your stupid cute mouth and eat the yummy fries, Anna!" Ruby bends the fries by stabbing them at Anna's lips. The comment surprises Anna and Ruby doesn't even notice.

"Fine!" Anna tries not to smile when she allows Ruby to push the fries into her mouth. But she didn't know Ruby would stick a spoon of milkshake into her mouth.

Anna splutters, the sides of her mouth with mostly whip cream. "Rubes, what're you doing?"

"Hold up." Ruby commands and covers her thumb with a napkin. She wipes Anna's mouth while feeling amused by the girl's annoyance.

Anna turns her head slightly and bites down onto Ruby's thumb gently.

"Hey!" Ruby dramatically jumps back towards her seat and against the window. "I didn't know angels bit." she jokes.

"I didn't know demons thought angels had cute mouths." Anna says under her breath. Her hands grip the wheel tighter at what she just said. She's surprised at herself, almost as much as Ruby is.

She can tell because it seems like both of them had sucked in a sharp breath of air before holding it till stepping into Castiel's home.

“Okay, um, shower arrangements.” Dean murmurs and squints, thinking, “We only have two showers, people come at six, and we all still need to cook.”

“We’ve got stuff!” Anna calls out waving the bag around. Out of thin air, Castiel’s grabbing the bag and suddenly appears into the kitchen again. She turns to Dean with a worried look, “Make sure he doesn’t stress too much.”

“I’ve got him.” Dean assures her.

“I have an idea.” Gabriel seriously states. They all look at him, knowing Gabriel is smart and actually cares for his family, “Castiel and Dean’ll be working on food longest, I need to clean up the mess from the baked yummies, and Sammich just got in the shower. I’m getting in right after him, so Anna and Ruby can share the bigger shower. The after that all four of us can tidy up, while you and Castiel take individual showers.”

“You’re a life saver, Gabe, you know that?”

“Yes, I know. You all should worship me.”  
 “Stop while you’re ahead.” Dean grins but it gets wider when they hear something drop.

“Dean!” 

“Coming!” Dean rushes to help Castiel.

“Wow, boyfriends cooking together.” Ruby jokes with a flat tone.

“You two should start, Gabe takes up all the hot water. Sam is generous.” Dean warns them.

“Got it.” Ruby heads to the hall.

“Hey, Gabe.” Anna stays for a second.

“Yeah, Anna.”

“I’m really glad you’re back.”  
He sighs, “Me, too, kid.”

She smiles with a little sadness caught in her throat. She turns to follow Ruby.

“So…..” Ruby is swinging her legs from over the bed’s edge. Her nails tapping against her thigh and her eyes blinking twice as fast then four times slower.

“You don’t-“ they both start at the same time. Both of them huff out a shaky laugh with smiles falling crooked.

Ruby starts again, “You don’t think this-“

“No, no. We’re friends, right?”

“Yeah, but I just want to know if you’re….”

“I’ve had sleepovers before, and I’ve showered with my friends and skinny dipped. It’s alright.” she knows it isn’t.

“My sleepovers must’ve been very different from yours then.” Ruby mutters, Anna still heard and they both feel hot and uncomfortable in the bad way, not the good way. “I can do a quick shower rinse and then you can go, we can make up a story about, you know.”  
 “Oh, yeah, yeah. That makes sense.” Anna nods. 

“Okay, I’ll start and…..yeah.” Ruby stumbles to the bathroom and the hot water feels like nothing compared to what her red face is feeling.

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

Anna waits a while, trying to calm herself down, and every time she picks up her phone, her fingers would twitch.

She gave up as the shower stop. She hears the handle turning, and she sits up.

Steam rushes out of the room followed by a more relaxed Ruby with a towel loosely fitted around her.

Water drips from her hair and down her thighs that are now paler in the winter than they were tan in the summer Anna first met the girl.

“You’re up.” Ruby’s voice, once again, breaks Anna’s train of thought. Anna shakes her head and blinks a couple times before looking up at an impatient Ruby.

“What’re you waiting for?” Ruby puts a hand on her hip and with the other she gestures towards the bathroom. Anna’s staring again. Ruby rolls her eyes and smiles, “Don’t worry, if you get in right away, the hot water’ll go to you first.”

“Okay.” Anna dumbly nods, sucking in her lips.

“Anna?”

“Yeah?” Anna looks up, Ruby shakes her head and starts to find her bag.

Anna stands up and tries to take a quick shower. It doesn’t work well at first, since she finds herself standing there thinking, realizing she’s zoned out again.

Once she notices, she quickly washes her hair and body, slowly stopping when she’s letting the soap fall out of her hair.

When she gets out, she makes sure to tighten the towel on her body.

Ruby’s wearing a light gray, dress that is square at the shoulders and looks, actually, comfortable.

Again, Anna doesn’t know how a girl like Ruby seems be elegant and blood-thirsty at the same time.

“You’re doing it again.” Ruby laughs.

Anna pulls up her towel and swallows back a blush, “Doing what?”

“The doe eyes. Those giant, round eyes staring into me like a window.” 

“I do that?” Anna tilts her head to the side.

“Yeah, is it a family thing?”

“I guess so. Castiel does it more often than any of us though.”

“I think it’s adorable.” Ruby smirks walking past Anna to get to the bathroom, at the same time pinching her cheek like a child.

Anna get’s into white loose blouse tucked into a light green skirt. The fabric is soft and Anna finds herself playing with the hems and her blouse buttons.

Ruby comes out of the bathroom with her hair brushed out nicely, parted down the middle like usual.

“Can I draw you?” Anna requests. Both of their eyes bulge out of their heads, “Sorry, I ju-“  
 “Yeah.” Ruby agrees before Anna can change the conversation.

“Yeah?” Anna leans in, as if she couldn’t hear correctly.

Ruby clears her throat and says more confidently, “Yeah. Where do you want me?”

“Just sit down and I’ll draw you in your dress.”

“I can put this dress back on without messing up my hair. Want me to just take it off? I’ll have everything else under.”

“I’ve never done figure sketches like this.”   
“I have. I wasn’t the drawer though.”

“Sure go ahead.”

Ruby slipped out of the dress very easily. Underneath is thin lingerie that are made of red and black lace.

“I’ll just sit….” Ruby points to the bed before sitting against the headboard. 

Anna sits crisscrossed right next to Ruby’s legs.

“You have a great figure.” Anna compliments, "I like your........under garments." What the hell, Anna? She thinks to herself.

"Thanks. You're vanilla, like your milkshakes."

"You guessed correct." 

"We can arrange that." Ruby winks and Anna really doesn't need this right now. Maybe she does, but not like this.

"Sorry, I already corrupted myself. But if I were to be corrupted a second time, you'd be perfect."

“Thanks.” Ruby replies with a laugh. There is a lot of silence besides the occasional sounds of the kitchen and the other shower. Also the strokes of charcoal against paper sound soothing. “Tell me about you family.”

“What do you want to know?” 

“Well, I’ll be seeing most of them tonight. Who am I seeing?” 

“You know Castiel, then there’s Gabriel and Lucifer.”

“What happened to those two?”

“Let’s just say this thanksgiving may be……tense.”

“Alright, who else?”

“Naomi and the douche, Zachariah will come. Uriel, Michael, Raphael, Hester, and Inias will come, as well.”

“Wow. Those names are just perfect.” Ruby laughs.

“Shut up.” Anna grins, “Talk to me, I really don’t want to hear my brother and Dean in the other rooms.”

“I doubt they’ll be doing anything. Their heads are too stuck in their asses to realize anything.”

“You’re absolutely right. Still, speak.”

“Nothing to talk about, actually. All my life has been full of journeys that don’t have adventures. I’ve got survival skills up my sleeves and I have a mental booklit of manipulation one-oh-one.”

“You’re terrible.” 

“You’re okay with it.”

“It’s because you’re not bad.”

Ruby snorts, “Really? I’m not bad?”

Anna looks up and looks back to her drawing, “You’ve done bad things, and you can be rude, but you aren’t bad. You’re helping me out right now, that means you’ve got a nice side.”

“You see, Anna. Out of all the sweet young things, you’re different. You give yourself a choice. Out of all the rotten hearted hotties out there, I’m different. I gave myself a choice. We both chose our minds.”

“We chose logic, despite how terrible we seem.”

“That’s out of pure fun.” Ruby makes Anna grin again, “I like your skirt.” Ruby tells her.

“Thank you. I don’t looks bad, do I? I haven’t seen any of my relatives in a while. How do I look, honestly.”

“Honestly?” Ruby repeats the word like she isn’t sure if Anna should know. Anna nods furiously like a child. Those deer-like eyes back at it again. Ruby sits up and crisscrosses her legs to mirror Anna. She isn’t great at voicing her wording sometimes, sometimes she is. Right now she’ll just have to find out, “Do you remember what I first said about your drawings?”

“It was yesterday, yeah.” Anna keeps on nodding. Her breath is heavy, and scared like a baby animal. Ruby doesn't even realize how naked she is when she leans in. For some reason it seems like a good idea to lean in to talk to Ruby. Anna's not complaining, if it weren't for the fact that Ruby is Ruby.

“What I said about your art is what I think of you. Not just right now, all the time. Not just looks either, inside and out.” Ruby admits.

Anna’s shaking stills and Ruby looks down at her hands. Ruby looks to Anna again, and is trapped by that stare. Anna isn't even sure how she's staring into Ruby's eyes that close without thinking about what Ruby is wearing.

Ruby’s not even going to scold herself for admitting that she thinks Anna is like her sketches.

 

Beautiful.

**Notes for the Chapter:**

> I might go back and add more. What do I need more of? Also, I was going to write more smut, but I'm not sure if anyone wants it. Which ship would you like to see more of and which genre? Thanks for reading my terrible, cliche writing.


	3. Anna's Angelic Family

**Summary for the Chapter:**

> Ruby finally gets to see Anna's terrifying family up close. Anna finally gets to face her terrifying family after a couple years.

Anna rubs her hair and head with the soft towel. She abruptly stops in mid-step when she spots the scene. It's like she crashed into an invisible wall, her face scrunched up and she steps back a little.

She thinks she should be used to this by now, that she's lived with this for too long. But, to make a point, she hasn't seen these two in five years or more.

Her hand still clutching the towel, her head tilted sideways, she glances over at Lucifer.

Her older brother stares lasers into the wall, she can almost see a hole burned into the wall next to the television, and, oh god, he's doing the hand thing again. Where he opens up his hands, fingers spread wide, then clenches them back up again.

Gabriel is doing the exact same staring, but at something else, and he has already managed to make the younger Winchester go red, unlike Lucifer and the wall.

Sam’s staring at the ground, not daring to look up because God knows what will happen if he sees Gabriel lick his lips or wink.

Anna clears her throat causing the tall young man to jump in his seat a bit. Anna laughs and lightly smacks Gabriel’s head, “Aren’t you a little too old to creep up on little boys?” with that Anna ruffles Sam’s long hair that is still damp.

Gabriel tries and whack Anna’s arm, but she moves aside. Sam changes the topic, “What took so long upstairs?”

“Please, Sam.” Lucifer doesn’t look back but continues to speak in a low voice, “I don’t need to know details about my little sister’s private life.”

“It wasn’t like that.” Anna’s voice goes a little higher than its usual pitch.

“I was joking, sis.” Lucifer rolls his eyes.

“Based off your tone, though….” Gabriel mutters.

“I was just drawing.” she truthfully answers, heading towards the kitchen for a snack. 

Castiel and Dean enter from the back door just to hear the words, “Her naked?”

And Anna’s response, “Only partially.”

“Excuse me?” Castiel looks taken aback.

Dean blinks before turning back to the door and leaving again.

“Oh, Anna?” Castiel hums.

“Yes.” 

“Would you and Ruby take care of guests until dinner officially starts? I do not believe they would be delighted to be greeted by Gabriel or Lucifer.” 

“Is that really needed, Castiel? Why can’t Sam or Dean do it? Is it not the same if I were to do it then for Gabe to?”

“You have Ruby. I see how relaxed you get near here. I would never ask you to do it on you own. If you’d like, I’ll have Gabriel also help you. But Dean is helping me and Lucifer would be the worst choice. No offense, brother.”

“I’ll pretend I didn’t hear that.” Lucifer cuts in for a second.

Gabe stands up right away to protest, “No way am I going to greet our dear old relatives. Do you remember the last thanksgiving we all had together?”

“Gabriel, if I’m going down, I’m dragging you along with me.”

“Either way, Gabriel, dear brother, I’m already labeled worst sibling, you can’t get any lower.” Lucifer comments.

Gabriel sighs, “Every time I think that, something goes wrong. I’ll be back in a few minutes.” Gabriel storms off.

Castiel looks down and exhales a heavy breath before walking out the door.

Anna looks towards where Gabriel rushed away and spots Ruby leaning against the wall.

Anna links Ruby’s arm onto her’s and drags them to the back yard.

After a while of silent fixing, Ruby speaks up, “Are you okay with this? Do you want me to talk more or anything?”

“Honestly? I think I just dragged you into a war.” Anna chuckles and buries her head into her hands.

Ruby gives her a genuine smile, pulling Anna in so she could swing her arm around the girl’s shoulders, “I’ve had my fair share in problems, this one won’t hurt. I’ve never actually seen Lucifer up close and in action, so that’ll be new.”

“You speak of my brother like he’s a machine.” Anna gives her an unamused exhale. Ruby just grins and pinches Anna’s cheek.

 

Anna glances towards Ruby before Gabriel speaks up, "I'll be there with you two if you need it."

"Thank you." Anna nods her head and sighs.

Walking out to Castiel's garden, Anna mutters to Ruby, "Sorry I brought you to a battlefield."

"I was okay with just knowing one of you, now I'm meeting the whole family." Ruby painfully laughs, "To them, I'm a walking and talking sin."

"Who says you're not?" Anna nudges her shoulder against her. Ruby smiles.

"Most good girls like bad girls, huh?"

"No, we're just two rebels attracted to each other apparently."

"Supposedly."

"Yeah." Anna tries to hide the faltering expression on her face.

"So, you left because you wanted freedom. You left and they want to take out anger on you now.

"Yes."

"Gabriel left because he didn't like the fighting."

"Yep."

"Lucifer got himself kicked out."

"I was too young to remember it. All I know is that Gabriel tried to comfort Castiel and I all the time. Then one day he left. He usually did, but this time he didn't come back. And I knew why, because Lucifer was kicked out right after the biggest argument I've ever seen between he and Michael."

"Family isn't always family. You can have siblings, uncles, aunts, but it's not always a family."

"But we were, we were."

"Are you sad, Anna?" Ruby stops to stand in front of her.

"I used to be." Anna doesn't look up.

Ruby moves her chin up, "What are you now?"

"Annoyed. Angry." Ruby grins at the answer.

"We're going to show them that you're the amazing person you are without needing them to raise you. Are you ready for that?"

Anna giggles and nods quickly.

"Good." Ruby makes a sound if approval.

 

~~~~~~~~~~~

 

She felt like an agent or a spy on duty. Plan 'Fake Relationship' was on and Anna felt excited. She's done worse but nothing that was as logical and fun as this.

It was also one that she can shove in her family's face which she appreciates the most.

Ruby and Anna kept looking at each other from different tables. Every time they caught each other's eye, they'd bite back a laugh and it just motivated each other to keep going.

The first person to come was cousin Balthazar and Naomi.

The two looked surprised to see her and she made sure they headed straight to the back. She'll have to get Lucifer and Gabriel to either help her or hide out until later.

"Anna, you're looking great." Balthazar compliments her. He spots Ruby, "Oh, a friend?"

She lightly hits him on the shoulder, "That's Ruby, my girlfriend. So play nice, Balth."

"Does she has a sister? Or a brother? Or preferably both?" he winks and she shakes her head. Ruby overheard and breathes out a laugh making sure it's not loud. He just chuckles at himself and joins Naomi to greet Castiel.

"Naomi, she means well. But she's also very....manipulative."

"Your whole family is like that." Ruby points out.

Next came Uriel and Zachariah, who give her deadly stares. Uriel giving evil smirks once in a while when Zachariah murmurs something to him.

"I got 'em." Ruby rubs Anna's shoulder with her thumb.

"Hello, you must be Zachariah and Uriel. I've heard some about you two."

"Some?" Zachariah questions. Anna feels intimidated by it.

Ruby just confirms it with a short nod of her head, "Yes. Don't you all own a company together?"

"Yes." Zachariah pretends to grin.

"Can you tell me, how do you become so successful? Well, I want to become wealthy at this young age."

"It takes a long time. Doubt you'll ever do it."

"I should ask Michael later. He is your boss, correct?"

Uriel starts to laugh and is given a cold stare from Zachariah.

"Hello, Dean, Castiel." Uriel looks over to the kitchen.

"Douche." Dean wants to flip him off.

"Mud monkey.” Raphael’s cold and low tone chuckles. This time Dean does flip him off.

 

~~~~~~~~~~~~~~~

 

"Anna, when did you two get together?" Balthazar asks.

"Like we said, we've known each other but it wasn't until recently I practically became Anna's new religion."

Anna wants to smack her head and laugh at the same time.

"Who confessed?"

"Ruby, of course." Anna puts a hand on top of the other girl's, "She kept a letter that she wrote and held onto it before she had the guts to confirm her love for me."

"For both of us, we knew we liked one another but our minds kept denying it." Ruby sighs.

"Ruby, you seem like an exciting girl, I'm sorry your significant other is my sister. She's very plain." He cups his hand so he looks like he'll whisper, "Probably plain in bed, too."

"I can assure you that Ruby will be teaching me lots of new things in this relationship." Anna replies to his comment.

"My student is eager to learn." Ruby playfully smirks and even though they can't see it, Ruby puts a hand in Anna's knee.

Anna rests a hand on Ruby's thigh.

"Naughty girls." Balthazar pretends to scold them. "It's a family dinner, for heavens sake!"

Raphael looks completely done with Balthazar's jokes and so does Zachariah.

Nothing really happens next until everyone is seated.

Hester, Inias, Hannah, and Gadreel stay together, them being most distant to Anna.

Uriel, Raphael, and Balthazar spoke somewhere else, mostly about business or family gossip.

One table in particular scared Anna, the one where her actual siblings sat.

"Anna," Michael says, "I was surprised seeing you here yesterday, but I had no idea Gabriel and Lucifer would show up. I need to catch up with you all."

"Michael, don't-"

"Why don't we talk? All together for a while?"

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

 

"You know, Ruby, you two don't seem to be in relationship." Dean Winchester states.

"You want video proof or something?" Ruby raises a brow.

"I mean I know you two are openly in love or something, I just don't think anyone here believes it."

"So like the opposite of you and Cas?"

"What? No!" he defends himself with a mutter of, "I don't like him." With that he walks away still reassuring himself.

Anna comes up to her next. She's about to put a hand on Ruby's shoulder but Ruby stops her.

Anna puts her hand back as if she burned it.

"Don't." Ruby grinds her teeth.

"What's wrong?" Anna innocently asks.

"What's wrong?" Ruby angrily repeats, "I'm scared! I'm more terrified then ever. Your family scares me more than anything. Plus, I've never even wanted to be in the same store as them. Now, every two foot radius is one of your relatives and I don't know how I let myself into this situation."

"Ruby, I've spent my whole childhood in a giant fancy house that seemed more like a jailhouse with these people in every room." Anna explains, "Why do you think I'm so angry with them? With me, it's just a free pass to mess with then without being afraid."

The pale girl uses her finger to make doodles in the center of Ruby's palm. "When you say it like that, it sounds fun."

"They can't do anything to me. They would usually, but with Castiel as the host, he won't let any of us fight."

"You know, angel, I can tell how you became such a clever, naughty girl." Ruby grabs Anna's swirling finger. "I just want to see the process in action."

 

~~~~~~~~~~~~

 

Anna’s walk wasn’t anything like Ruby’s determined stride. Ruby’s walk cleared hallways, it had people take a step back. Anna’s made people stop to stare in curiosity. 

This time, Anna was dragging Ruby across the grass garden. Ruby’s expression seemed satisfied, happy, and plain old excited.

Anna’s face always seemed like she was staring into a portal of a realm no one else could see.

And the way the two walked together was like a collision of complete confidence and total determination. The two were a solid bulletproof couple side by side.

Anna’s arm walk was loose, as usual, but her arm that took Ruby’s is sturdy.

Everyone was here now. Everyone hadn’t seen Anna yet and she didn’t stop to explain herself.

Her gaze is locked on her targets, her siblings.

“Is that Anna?” she could hear every two seconds, “Who is with her?”

She faintly heard Balthazar explaining, which she’ll have to thank him for later unless he added something that’ll make this situation worse.

“Is it usual for Thanksgivings to be so separated?” Ruby eyes the different tables.

“In this family, I’m glad we’re all grouped like this.” Anna doesn’t tear her eyes away from the spot where they’re heading.

The circular table is mostly filled with boys. It isn’t her fault that she’s the youngest sister, although Michael did look as young as Anna did.

There are no ends or points of a circle, but her brothers made it into a triangle shape. Every chair or so sat Michael, Lucifer, and Gabriel. The other chairs filled with Castiel, Dean, Sam, and two other girls.

“When did you two get here, Gabriel, Lucifer?” Michael asks.

“About four in the morning.” Gabriel replies. Michael isn’t really paying attention to what he’s saying. He is watching Lucifer’s silently angered expression with a sad smile.

“Did you two come together?”

“I didn’t even know he was coming until we showed up at the door at the same time.” Gabriel speaks with a grin and Anna is pained by the hurt behind it.

“Oh.” is all Michael can manage to say or even think of.

It’s silent. It’s not even that bad, Anna believes. Maybe it’ll be like this for the rest of the night.

Or maybe they all somehow still have that bond that tells each other what they’re thinking because one second it’s uncomfortable for everyone else and one second it’s, “You know I had to change my name at least three times because your men found me again and again?” Gabriel pointed at Michael.

“You shouldn’t have ran then! We were all hurt that you did!”   
“I wanted you two to stop fighting!” 

“How do you think it felt like getting kicked out and not seeing you? I got to at least see my whole family’s faces before they shunned me! I never got to see you.”

“Well, sorry. Maybe if some shithead didn’t ruin the family in the first place, I wouldn’t have walked out before someone else did. Oh wait. Those two are the same person! You, Lucifer, it’s you!”

“All I wanted was for us to unite together and become strong together! Don’t you see that I just wanted all of us to be a normal, happy family!”

“I understand that, Lucifer. Your intentions are at the right spot, but the way you did it was cruel and terrifying!”

“Don’t start with that, Michael! I-“

 

“Hey!” Anna yelled and Ruby’s lips didn’t hesitate to smile. She can tell by the feeling of Anna’s hands that she felt great to yell.

The girl sitting next to Lucifer looks pained that the argument ended.

“Anna?” a women with sunglasses and a black tank top calls out.

“Pamela.” Anna mutters. The blind woman smiles and Anna’s face lights up.

Ruby looks between the two girls in a confused and slightly hurt manner. Maybe it’s because she liked seeing Anna finally stand up to her family after pretending not to be with them. Just like Gabriel had, except Gabriel was just screaming his feelings out.

The girl who had liked the bickering stands up to take a look at all of Ruby. The girl licks her lips and smirks beautifully.

The strong pressure of Ruby’s grip makes Anna go back into her thought process.

“Good for you to join us now, Anna.” Castiel nods for Anna to sit down.

Anna doesn’t let go of Ruby’s hand while waiting for Ruby to sit down first. Then Anna sits, making her chair close to Ruby.

Ruby lets go of Anna’s hand to put it around the redhead’s waist then moving her own farther arm to play with Anna’s delicate fingers.

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~  
“Did we miss anything?” Ruby cocks her head, ignoring the whole accusing game that just played out.

“No, no.” surprisingly Lucifer answers her, “We just started to have a nice topic.”  


Anna almost stabs her fork into the plate and cracks it.

“It’s you all.” Ruby relaxes her own shoulders, “Meeting the family is always pretty scary.”

“You’ve met me before.” Lucifer pouts and how does a devil’s child looks so innocent?

“Yeah.” Ruby nods, “And I’m still scared.” Gabriel almost spits his water out.

“How’s life, sis?” Gabriel asks.

“Good.” her eyes flicker to Ruby, “How about you? Are you interested in anyone?”

“Nope. Its kind of weird, no one’s caught my eye lately.” Gabriel shrugs, “It’s gotten boring.”

“What happened to Kali?” Michael wonder out loud.

“They broke up. It was the only real relationship Gabriel has had, so it was unfortunate.”

“She dumped me, right after Lucifer destroyed her property.” Gabriel glares at said brother.

“It wasn’t my fault.” Lucifer doesn’t seem to feel apologetic about it.

“That was you?” Ruby exclaims. She leans over the table to high five Lucifer. Lucifer nods in approval at Anna.

Michael raises his eyebrows at that.

“If Lucifer approves, then we must all be doomed.” Gabriel jokes.

“What does that supposed to mean?” Lucifer angers.

“You know exactly what I mean.”

“Isn’t it odd, “ Lucifer smiles, “that all of us went our separate ways? We used to be a family.”

“Lucifer, enough.” Castiel calmly tells him.

“Even sweet Castiel. I believe he’s the real rebel out of all of us. I mean, first glance, Castiel wouldn’t be considered a rebel. But, oh, he is. At least Gabriel stayed out of it, Michael’s on one side, I’m on the other. Anna isn’t even part of the family anymore. Castiel, though…” Lucifer looks over at Michael.

“He’s brave enough to invite all of us.”

“I want exactly what you all want, to be a family once again. Can’t you see we all want the same exact thing?”

“Castiel, I should know what it is like to be with people outside our family. I mean, Gabriel understands it as well. But he’s never felt it. I have. But you, brother, you’ve chosen it over family. You want both. You can’t have both.” Anna tells him. Ruby stares up at her with lust and admiration.

“If I stick with family, how will I ever live life? How will you all?” Castiel argues.

“We all always come back to where we started, you will, too. I don’t know why you still continue to change things. You can never change things, brother.” Anna confirms with a demanding tone. Ruby holds down a smirk and a laugh.

“Anna, you shouldn’t say such things.” Gabriel looks over to Castiel.

“But it’s true. I’m right.” Anna yells.

“Yeah, you’re right.” Lucifer agrees, “Which means Ruby’s just another phase of yours.”

Michael smiles. 

“It’s just another one of your getaway plans.” Lillith shortens the explanation. She steals another look at Ruby.

“You can just tell me if you don’t like Ruby. You don’t care about her? Good. You like her? Great. If you hate her, well, “ she darkly chuckles and Ruby crosses her arms and bites down a smirk, “its perfect.”

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

 

 

 

 

“For pretending, you do a terrible job, Anna.” Gabriel tells her in the kitchen.

“Shut up.” Anna steals his chocolate bar, a love they share.

“Listen, Castiel’s letting me invite friends, I’m playing matchmaking for all of them while have a little fun for myself. You in?”

“By matchmaking, do you mean Castiel and Dean Winchester?” 

“Of course I do, plus there will be booze and lots of other fun activities.” he winks.

She shakes her head and rolls her eyes.

“Hey.” he shakes her shoulders, “It’ll be good practice for you and Rubes.”

“Do we fake being in love that bad?” Anna fake whines.

“No.” Gabriel turns on his heel to face her, “You two are bad at pretending it’s pretend.”

With that, Gabriel walks back outside and leaves Anna to think once again.

**Notes for the Chapter:**

> I'm sorry this is a little late. I'm writing another Annaby au fic. It is going to either be Little Red Riding Hood or Persphone and Hades. You can leave a comment saying which one I should do. I am also deciding to write an Adamandriel (Adam/Samandriel) fanfiction. This isn't my best writing and hopefully you still leave kudos and comments. Be sure to write CROATOAN somewhere on your body today!


	4. You Love What You Meant To Hate

**Summary for the Chapter:**

> Ruby finds herself feeling out of place with all of these friends. Then unexpected but expected things happen. She's just glad she's not as oblivious and in denial as Mr. Dean Winchester.

Ginger and honey fly around in strands. Jo is laughing on the couch trying to make Dean trip while he’s fighting Charlie, the two best friends slashing plastic lightsabers together.

 

Anna had thought about this randomly. Charlie Bradbury is the sister Dean Winchester never ever wanted and Jo Harvelle is almost like a relative he grew up with. So who will Dean be more protective over when he finds out the two might like each other?

“Charlie? Jo?” Ruby expresses confusion because she is sure she saw them in a different state just a couple days ago.

“Hey, Ruby.” Jo waves as she watches in amusement as Charlie beats Dean at swordfighting.

"Why're you two here?" Ruby asks.

Charlie whines, "We just wanted to join the love fest!"

"What?" Dean gives the two odd looks. The girls respond with a fit of laughs.

“When’d you two get here?” Ruby ignores the comments.

“Charlie took me to my first convention.” Jo grins, a blush appearing. Luckily her blonde hair covers up her ears and cheeks.

“Then Jo took me out to her great shooting range.” Charlie explains between swings.

“How’d that go?” Dean smiles over at Jo like he knows exactly what Charlie is capable of. Mostly because he does.

Jo pouts, “Well, I thought I could play badass and show her my awesome skills, but someone had to be perfect all around.”

“Please,” Charlie snickers, “Jo Harvelle, you were completely turned on when I didn’t miss a single target.” She pokes the lightsaber at Jo’s stomach. Jo grabs it and pulls it to get Charlie to come closer.

Ruby glances at Anna and the two exchange thoughts and laughs with just eye contact.

“Where’s Sam?” Jo looks around.

“Probably sighing and pining over a Novak.” Charlie answers, “He follows your footsteps, Dean.” she jokes.

Dean just rolls his eyes, never seeming to bother and deny it anymore. Then the gears churn in his brain, “How do you know about Gabe?”

“I’ve seen him around in conventions and LARP grounds before. Last year, he found every trick and advantage to use on our side. He led my army into victory without having to stop character, the dude is cool.” 

“Who knew he was such a nerd? No wonder Sammy’s fallen flat on his ass.” Dean groans.

 

~~~~~~~~~~~~

 

They are all huddled outside in small group conversations waiting for Gabriel to come back with drinks. Ruby didn’t know how to feel exactly. She didn’t feel fit in here.

 

“Hey there, Rubes.” Meg appears next to Ruby. Ruby is slightly startled.

“Meg, I didn’t know you were coming.” Ruby crosses her arms tighter to herself.

“I couldn’t resist a night with Lucifer, Lilith, and you. All we need is Alistair and the whole group will be back together.”

“Won’t Azazel be proud.” Ruby smiles and it’s an evil one.

“Oh, Dad would be. He does adore Luci, you know.” It is true. Meg's father worships Lucifer as much as Meg does. Meg's round face grows softer, "How've you been?"

"Why would you care?"

Meg sighs, trying again, "How's that unicorn of yours?"

"She's talking to the great Pamela over there." Ruby doesn't even nod her head towards the two said girls. Meg looks over at Anna smiling and nodding like a naive young schoolgirl listening to a hot math teacher.

"You jealous?" Meg's lips twirl into a smirk.

"I think it's supposed to be a good thing I'm not talking to any Novak's." 

"You mean Milton's?" 

"Novak, Milton, Shurley, I'm not even sure anymore." Ruby says quickly, meaning that isn't the point.

"Who cares about her?" Meg shoves Ruby, "When was the last time all of us were together? We need to have a little fun."

Ruby raises an eyebrow, "I'm not burning down a building with you."

"That was your idea in the first place." Meg reminds her. Ruby waves the importance away.

"Meg!" Gabriel's voice sounds delighted, "Here for my little brother?"

"Sorry to Clarence, but I'm here for Luce." Meg grabs the drink from Gabriel and takes a sip.

"I always knew it was more of a cult than a gang." Gabriel sets off memories of high school in their minds.

"You went to school with my brother?" Anna overhears.

"Yeah." Ruby's surprised at the angry tone of voice she hears come out of her own mouth. It seems Anna is more on the confused side.

"It used to be fun." Meg smiles at the memories. Ruby scowls at them. "Lucifer leading us with Lilith always by his side. Too bad for young Ruby, she had a major crush on her-"

"Shut up, Masters." Ruby slaps a hand over Meg's mouth but only gets pushed away. The slapping sound startles the others and the push is more of a punch to the gut. Anna doesn't know whether to be surprised or used to the violent actions displayed.

"Anna, how come you were never sent to our school?" Ruby asks, "You would've scared the crap out of everyone, that place is full of future villains."

Anna does not know if that was a compliment or not, "I'm not sure, although I would like to see Lucifer's high school gang back then."

"You can see it now." Lucifer tells her and he gesture towards Meg, Ruby, and Lilith. 

"Not much to see, is there, Luce?" Anna grins around her drink.

 

~~~~~~~~~~~~~~

 

Somehow, after a couple of drinks that Castiel and Gabriel put together (which probably consists of alcohol and sugar only because Castiel's amount of shots to get him hammered is large and Gabriel does not get drunk unless sugar is involved), Meg had convinced Ruby to go on a ride with them.

"Where are you all going?" Dean asks, leaning on Castiel.

"We're going out. Reunion, remember?" Meg answers vaguely.

Ruby slides her arms into her leather jacket and watches Anna. Surprisingly, or not, Anna's looking confused at Ruby.

"Where will you be?" she asks them all.

"No where you need to know, princess." Meg smiles. Anna clenches her fists. "Or heard of, probably."

"You two coming?" Lilith rolls her eyes, her arms linked on Lucifer's.

 

~~~~~~~~~~~~~~~~~~~~

 

Once Ruby left, Anna didn't talk anymore and found herself bored by the conversation. It surprises her that she keeps being distracted by the thought of Ruby. Gabriel and Castiel were always great to talk to until this point.

"Worried about Ruby?" Dean asks.

"No." Her hands clench in anger.

"Are you sure? You don't seem well." Castiel observes, "You know it is fine to show your emotions for Ruby. She is your girlfriend."

"Please, brother, just be quiet." Anna gives a stern look and gets up to walk to the kitchen.

Refilling her glass and tipping her head back so the liquid can go straight to her throat, she gets a little more irritated.

Half of her is filled with annoyance. Annoyance from her family, from this trip, from the world, from everyone she's ever laid eyes on.

The other half of her feels like it is pining after something. She's got these longing thoughts in a raged mindset.

Why the hell did her family have to come back into her life? She should be used to it by now. But at the same time, it sucks every time they come back or she comes back.

Why did Castiel have to go and invite everyone? She feels fear and anxiety whenever she faces them. But this time it was different. This time she felt confident, she felt done with their shit. She always has, but now it shows. It's because of Ruby.

God damn that girl. Anna's life was simple away from her family and never meeting Ruby.

Oh, but Ruby is the most exciting thing that's happened in Anna's life. 

Ruby unlocks a door to more emotions Anna never thought she can have. The reason she left her family, because they would've turned her into a heartless douche.

Ruby didn't give Anna any personality traits or newfound thoughts. Anna just felt more open around her. In public together, she felt open in a strong way. She felt invincible to anyone's words or judgment. 

Alone with Ruby, she also felt open. But she it was a soft kind of open. She felt cared for and like she can say anything. Ruby makes her feel vulnerable when they're in private. But Ruby never makes her feel weak.

 

~~~~~~~~~~~~~~~~

 

 

Meg's idea of a 'reunion' is bottles of vodka at their favorite spot back when they were younger and needed to actually hide booze.

Ruby starts to feel her mind float above her own head. When Lilith asks why she's zoning out, they all tease her about Anna. She doesn't like Anna. She does not like Anna Milton whatsoever.

But she can't help but like it when Anna works with her. She'd choose Anna over anyone as her partner in crime. If the two were still in high school, they'd be the perfect power couple. 

With Lilith, Ruby obsessed over the idea of her. She praised the idea of Lilith being hers because in her eyes back then, Lilith was a god. But now? Ruby finds herself adoring Anna more every glance they share.

Ruby likes Anna, not what she can do with her or the way they fit together. It's those little facts and more. She likes the way Anna can have her head in the clouds and it makes Ruby feel like she needs to protect Anna and wrap her in a blanket. Other times, Anna seems like the only one with their head in the right way. Ruby sometimes thinks Anna is the only one connected to reality. Anna is strong and knows what she's capable of.

Ruby wants her both ways. She likes the cheerful Anna and the badass Anna. She likes the way Anna zones out. She just likes the way Anna thinks, acts, talks, walks, how she yawns, how brave she is, how-

Holy shit. 

Ruby likes Anna Milton.

Ruby. Likes. Anna Milton.

 

~~~~~~~~~~~~~~

 

Once a bottle, or two, is gone between Meg, Lilith, and Lucifer, A while ago, Lucifer says he is going to buy more drinks or invite more people. Right now Lilith is technically 'in charge'. 

Also, Ruby has never been more pissed off at her friends.

Actually, she's just never been more pissed off at Lilith.

Lilith and her pretty long blonde hair. Lilith's persuasive words and hypnotic body. Her determination and her pureness even though Ruby knows Lilith is the most unholy person she's even known.

Ruby feels her phone vibrating. She checks the notification with Meg looking over her shoulder. 

Come back soon? Code: Fallen Angels. It's okay if you don't though. Have fun.

"Code fallen angels?" Meg questions.

"It means a family disaster is happening." Ruby explains, she's pretty sure Meg is the most loyal and trustable person she knows.

Plus, it wouldn't matter. Meg doesn't need this kind of information.

"Hey, Lilith." Meg tells the blonde. Lilith turns to her, "Take us back home?"

"Why? We're just about to have fun."

"We'll just drop off Ruby."

"Ruby?" Lilith turns to said girl. "Why're you going? You don't want a reunion?" With each step, Ruby's breath hitches. Lilith is invading Ruby's personal. Ruby is sure that if she didn't like it, she would've already stepped away.

"Lilith, stop it." Meg stands in between them. "Anna needs her. Let them be."

"Anna? Really, Ruby? You went from me to Anna?"

"We will talk about this later. I promise I will right after you take me home for a while." Ruby crosses her arms and a hint of a smile shoes. "Then we can keep on chatting, or use our mouths for better use."

Lilith grins and pulls Ruby against her chest. Their breaths quick and off beat.

Meg tugs on Ruby's arm and drags them to the car.

 

~~~~~~~~~~~~~~~

 

Meg and Lilith were forced to wait outside where Sam and a Dean were waiting as well.

Ruby didn't listen but they managed to slightly convince her. That is until Ruby heard Anna's voice and then ran into the house.

Ruby wished she hadn't. She wishes she didn't see the Novak family up close and in action.

"This always happens! Every single fucking time!" Gabriel yells at his two older brothers, "I bet you aren't even listening to me!"

"This is none of your concern, Gabriel." Michael calmly says.

"None of my concern? Are you serious right now?" Gabriel runs his hand through his hair is anger.

"I agree with Gabriel." Anna speaks.

"You're agreeing with the brother that left us when the family was starting to tear apart. Shouldn't he have stayed and helped you? Shouldn't he have been the big brother he wanted?" Lucifer's rises.

"You're telling me I should've been the good big brother? What the hell are you two then? Whiney assholes?" Gabriel looks furious.

Lucifer cocks his head to the size, "Whiney asshole? That's no way to speak to your family."

"We were family. We were. I can't call any of you family anymore. Not because I loathe you all but because we're not a family if one piece is broken. Hell, we're all broken pieces. The puzzle doesn't even fit anymore." Gabriel's voice sounds heartbreaking.

Lucifer has a sad frown, "Gabriel..."

"No! Don't do that to me! Don't, Lucifer."

"Lucifer." Michael warns him.

"You were the one that had to kick me out. After that, what happened? Hm? Did you take care of them ever?"

"Of course I did-"

"That's not how I remember it." Anna scoffs.

"Go on." Lucifer nods.

"Sure, Gabriel ran away. But he got away for good. Me? I left and they only wanted me back just to ditch me again. They just wanted to teach me a god damn lesson. If they didn't want me, they would've let me go! But they don't! Our relatives force me back into the family so they can push me out of it again."

"On your watch, Michael, you have had two of our siblings run away. I would have never let that happen."

"Well, what would you have done that I couldn't have?" Michael asks.

"I would have tried everything to make their lives better than I had it."

"You think I never tried? I had tried my hardest." 

"Stop it." Castiel quietly orders. They all ignore him.

"I was shunned for my whole life!" Lucifer yells.

"Everybody loved you!" Michael argues.

"It's been years and you all still haven't changed." Gabriel chuckles and Ruby feels downright pained.

"You both are assholes, how about that?" Anna yells over their yelling.

"Watch it, Annael." Lucifer threatens.

"And you're supposed to me arguing over who's the bad brother." 

"Don't do anything stupid." Gabriel comments.

"You mean like when you ran away so you wouldn't have to face responsibility?" Anna knows it's mean and it's not true but she doesn't care.

"You mean like you tried to pretend you weren't part of this family?" Michael asks.

"No one would want to be part of this family."

"Way to be a good brother, Michael. You fucked Anna and Castiel up. I can take partial blame on Gabriel but-"

"Lucifer, I made you leave once and I will do it again."

"Stop." Castiel repeats and it sounds pleading.

"You never loved me."

"I did. I really did." 

"Screw you, Michael!"

It was quick but Ruby's seen it many times before to not know what just happened. 

Lucifer would never be crazy enough to actually hit Michael with the glass bottle. But he threw it at the wall beside his brother and glass shattered.

With that, Lucifer walked out of the house and Ruby can hear the faint engine roaring in the silence.

Gabriel storms out after the car is gone. Michael leaves in his own car. Anna goes into her room. 

"Ruby?" Anna didn't even know she was here until Ruby opened the door to their bedroom. "How much did you hear?"

"Enough." Ruby sits at Anna's side where the girl is curled up.

"It's happening all over again." Every word Anna says is choppy like its own sentence. Her breathing is rigid and her voice cracks. "I-I fucking knew it." Anna's hands grab her head and hair, pulling and tugging at her red locks trying to stay calm.

Her nails dig into her skin and she must be pulling out strands.

Ruby pulls Anna's arms from over her head, "Anna, it's-"

"Okay? No it is not! I knew this would happen. I'm so stupid. Why the hell did I bother showing up?" She shrivels up even more, curling, holding her legs to her stomach. Ruby feels pain seeing her like this. The sadness quickly becomes anger. The tearing up eyes stop and rage fills the room.

"Anna, breathe. Breathe, Anna." Ruby tries to make peace.

Everything then stops. The tension Ruby felt, it's not there anymore. Anna sits up, turns around to look at Ruby. She zones out again, that thing she always does like she's looking into another dimension no one can see. "I'm done."

Ruby almost flinches when Anna's eyes meet her's. They both feel trapped in the gaze. Anna smiles, "I am not dealing with their shit anymore."

Ruby puts her hand on Anna's knee, Usually Ruby would rub her thumb on the girl's knee to comfort her. She does this now but Anna doesn't need comfort. But she does need Ruby. Ruby grins that mischievous smile that caught Anna's attention in the first place. Ruby speaks, "Everything is black and white for me. I hate what I hate and I love what I love. The thing is, you end up hating what you love. I end up loving what I was supposed to hate."

Anna lock her fingers together against the back if Ruby's neck and she pulls herself upright. Anna is brought up to Ruby, face to face.

The way Ruby kisses is fierce and rough. All of Anna's past boyfriends were passionate and slow. They made sure every little detail was perfect. With Ruby, the two girls grabbed what they want and took what they need. Anna though Ruby would always be the one with dominance. 

She realized that Ruby did have control without controlling anything. Ruby is irresistible to her. It makes Anna want to throw her against the wall and kiss her like a ragdoll. Ruby let's her.

Anna is being the rough one, but she'd also be the needy one.

What the two didn't expect is that Ruby is actually just as needy. 

Ruby always had partners that craved her. She did not think Anna Milton would be the one that makes her melt with one kiss.

"What's going to happen to you and your relatives?" Ruby smiles, forcing the answer out of her. Anna is pinned against the headboard, slumping against giant pillows.

Anna pushes herself up and pushes Ruby down before answering seriously.

"I'm going to make sure they know I want out if this family."

**Notes for the Chapter:**

> I'll start posting more, I've just been working on other fics that I have. Check them out? Also leave comments? Thanks


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